It's the second day of Drake Clifton's three-day Outward Bound solo, and he's starving. He rattles his small food bag in front of the camera: crackers, nuts, a nub of cheese. Matted blond hair pokes out of his black beanie. "It's seriously killing me," he says, pouring crumbs into his mouth. He's camped in a boulder-strewn basin high in Colorado's Sangre de Cristo Mountains, with no books, no watch, no companions. His course, a 22-day mountaineering trip for 16-to-18-year-olds, is almost over, and he and his classmates have been separated to sit and reflect on life. He aims the camera at his knuckles, on which he's written "feel love and joy," then peeks out from under the tarp at the gray sky. "Part of the experience is to feel lonely, hungry, just have time to think about stuff," he says. But by the next afternoon, he's sick of it. "I'm so bored and I'm drawing the most pointless stupid fucking picture right now," he says, panning to a swirly drawing of an octopus-man. A few weeks later, though, underneath the YouTube video he posted of his solo, he will write, "I look back at this and I am so proud I got through it."

Everyone's "Outward Bound moment" is different. For Morgan Lane, it was struggling to carry an 80-pound canoe on her shoulders during a portage in Minnesota. For Jasmine Myles, it was climbing to the top of a rock wall in Colorado, despite her disabled arm. Outward Bound puts students in unfamiliar, challenging environments to help them realize there is more to them than they know. "Saying this experience changed me would be a huge understatement," Lane said in her own YouTube video. "I was liberated."

Outward Bound has instilled confidence and self-awareness in over a million participants since its first U.S. course in 1962, making the nonprofit a household name and spawning an entire industry. Former instructors have created some of OB's biggest competitors, including the National Outdoor Leadership School, where founders of programs like the High Mountain Institute and Deer Hill Expeditions received their own wilderness training. In 1987, President Ronald Reagan even proclaimed a "National Outward Bound Week."

But OB's legacy hasn't kept it out of trouble. The national organization lost money and enrollment for years before nearly collapsing in fall 2011, splintering into individual schools. Suddenly, branches of the country's oldest outdoor education school were scrambling for cash –– sending out desperate Facebook pleas, even selling old canoe paddles to pay the bills. "At first, it was like, oh my gosh, Outward Bound is going to go away. Here we are in our 49th year in the U.S., and we're done?" says Nancy Crane, a 17-year employee who's now operations and safety director at Colorado Outward Bound School in Leadville. But slowly things improved. Instructors went into the field with students, donations rolled in, and morale rose. Now that the crisis has passed, Outward Bound schools nationwide are asking themselves tough questions: who they are, what they do, and how to stay relevant in a world that they feel still needs them, whether it knows it or not.

The name "Outward Bound" comes from the nautical term for a ship leaving safe harbor for the open sea. Teacher Kurt Hahn founded the school in Wales in 1941 to give young boys, many of them sailors, the fitness, tenacity and teamwork they would need to survive the war and thrive in their jobs. The idea caught on, and schools sprang up around the United Kingdom, eventually reaching the U.S., where Hahn-protégé Joshua Miner started a school in Marble, Colo. On the first course, 35 boys spent 26 days learning knot-tying, rock climbing and orienteering. They summited a 14,000-foot mountain, ran for miles and spent one night alone, the forerunner of the iconic "solo."

By the end of the decade, OB had grown. Schools in Minnesota, Maine, the Northwest and North Carolina sought to teach through wilderness rather than about it, using the natural environment to cultivate character and encourage teamwork. The boys came back both fitter and more confident. One parent wrote: "His Outward Bound experience has taught him to meet challenges with an assurance he never had before."

Early support in the U.S. came from prep schools, but OB's founders also wanted to reach out to low-income urban kids. Teenagers from different backgrounds camped and lived together in what became an integral part of the experience. "It's not just a heavy backpack or portaging a canoe," says Paul Duba, a 27-year Colorado Outward Bound School veteran instructor. "That cultural challenge is every bit as much (a part) of the thing they're overcoming." But staff worried about what happened when those underprivileged kids went home. "We take kids from tough circumstances, give them a great experience, and then drop them back where they came from. Surely that can't be enough to make a difference in a high percentage of cases," Greg Farrell, who helped the organization expand into cities, told the authors of Outward Bound USA: Crew Not Passengers, the school's official history. In the 1980s, OB began building urban centers. Doing a ropes course in Boston or canoeing up New York's East River blurred the line between the "real world" and the challenge of the outdoors. The organization even designed and implemented a public-school curriculum.

The transition redefined Outward Bound, however, and not everyone was on board. In 1994, the University of Colorado assessed OB's urban and public school initiative and found that "some wilderness veterans, for example, are struggling with the idea of being able to provide an 'Outward Bound experience' without the physical demands of a 26-day expedition." Even as OB grappled with internal conflict, the outdoor education market was becoming more competitive. New programs popped up around the country, and others, like the National Outdoor Leadership School, became more popular. Ten years after Reagan's National Outward Bound Week, enrollment had dropped and revenues were flat. "Among the cognoscenti, Outward Bound isn't the brand name of the industry (anymore)," Robert Gilpin, author of Time Out, a book on alternative education, told The Wall Street Journal in 1997.